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CDC Reaction Involving α -C-H Bonds of Nitrogen in Amines 李南 2012.6.16.

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Presentation on theme: "CDC Reaction Involving α -C-H Bonds of Nitrogen in Amines 李南 2012.6.16."— Presentation transcript:

1 CDC Reaction Involving α -C-H Bonds of Nitrogen in Amines 李南

2 Yoshida, J. Am. Chem. Soc. 1999, 121, 一般形式

3 Murahashi, S.-I. J. Am. Chem. Soc. 2003, 125, Murahashi, S.-I., Angew. Chem., Int. Ed. 2005, 44, Murahashi, S.-I., J. Am. Chem. Soc. 2008, 130, Conditions A: 2.5 equivH 2 O 2 ; Conditions B: 60 o C, 1 atmO 2.

4 Ofial, Chem. Commun., 2009, 45, Bir Sain, Chem. Commun., 2009, 45, Zhu, C.-J., Chem. Commun., 2011, 47, 2354.

5 Li, C.-J. J. Am. Chem. Soc., 2004, 126,

6 Fu Hua, J. Org. Chem., 2008, 73, Li, C.-J., Org. Lett., 2004, 6, Li, C.-J., Tetrahedron: Asymmetry, 2006, 17, 590.

7 Pierre Vogel, Org. Lett., 2009, 11, 1701.

8 Li, C.-J., J. Am. Chem. Soc. 2005, 127, 6968.

9 Huang, Z.-Z. Org. Lett. 2010, 12, Che, C-M., Chem. Commun. 2010, 46, 2739.

10 Ramaiah Prabhu, Chem. Commun., 2011, 47,

11 Kawakami, Y., Angew. Chem., Int. Ed. 2004, 43, 4231.

12 Itami, K., Chem. Asian J., 2009, 4, 1416.

13 Li, C.-J. J. Am. Chem. Soc., 2005, 127, Li, C.-J. Green Chem., 2007, 9, Conditions A: ∼ 80 equiv nitroalkane, equiv t BuOOH; Conditions B: 5 equiv nitroalkane, 1 atm O 2, H 2 O, o C.

14 Stephenson, C. R. J., J. Am. Chem. Soc. 2010, 132, 1464.

15 Zhu, C.-J., Angew. Chem., Int. Ed. 2012, 51, 1252.

16 Li, C.-J. Green Chem. 2007, 9, Li, C.-J. Eur. J. Org. Chem. 2005, Conditions A: 2.5 equivH 2 O 2 ; Conditions B: 60 o C, 1 atmO 2, H 2 O.

17 Mikiko Sodeoka. J. Am. Chem. Soc. 2006, 128,

18 Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075.

19 Wang, Rui, Angew. Chem., Int. Ed. 2011, 123,

20 Klussmann, M. Chem. Commun. 2009, 45, Guo, C-C., Chem. Commun. 2009, 45, 953.

21 Magnus Rueping, Chem. Commun., 2011, 47, 2360.

22 Chi, R. Y. Angew. Chem. Int. Ed. 2012, 51, Klussmann, M. Synlett 2009, 10, 1558.

23 Huang, Z.-Z. Angew. Chem., Int. Ed. 2010, 49, X= O, S, CH 2, (CH 2 ) 2

24 Conclusion 1. Although using simple and inexpensive building blocks is an attractive alternative to consuming more functionalized and costly reagents, chemo- and regioselectivity remain issues that limit the broad usage of these methods. 2. Practical approaches to C-H bond oxidation using reagents that are more environmentally friendly, such as oxygen, electricity, and visible light, are desirable and are being developed. 3. In terms of asymmetric catalysis, enantioselective C-C bond formation by C-H bond oxidation is still in its infancy, although ligand-accelerated transition metal catalysis and organocatalysis has enabled some growth.


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